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Great leadership is not a skill. Leadership relies on values and attitudes. Here is one attitude that every great leader has.

Every month I have dinner with a group of local executives and entrepreneurs. Ostensibly we gather to discuss an assigned reading, but more often than not the conversation devolves into sharing “war stories.” At one meeting, a highly successful serial entrepreneur told us that upon graduating from high school he decided to take a couple years off, travel the country, and “grow up a little.” Every time he was ready to move on in search of fresh adventures, he would head to the pilot’s lounge at the local private airport. Parking himself near the telephone, he would eavesdrop on pilots as they called in their flight plans. If one of their destinations caught his fancy, he’d approach the pilot and ask if he could tag along for the ride. More often than not the pilot would gladly comply, and our intrepid hero ended up flying all over the country for free.

He went on to say that he owed all of his later business success to hitchhiking through the clouds. The pilots turned out to be a highly successful and fascinating breed, and he learned a lot about life and business by just talking to them. Several, impressed by his initiative, helped him find a job and a place to stay after they reached their destination. A couple became valuable lifelong mentors and contacts. But most importantly, the hours he spent hanging out in pilot’s lounges taught him that with initiative and determination just about anything is possible, and this all important lesson was critical to his later success.

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More often than not when highly successful people gather the conversation turns to war stories, and I’ve noticed that the common denominator to all these stories is the story teller’s ability to hustle. People addicted to hustling spend little if any time wishing the world was “fair.” Instead like an investor determined to beat the stock market, they rely on the social inefficiencies that others bemoan and turn them into golden opportunities. Hustlers seek life’s toughest challenges just for fun, and they like nothing better than being told “You can’t do that!” just so they can vigorously retort, “Oh yeah? Just watch me!”

Successful hustlers are forever pushing the envelope and searching for “angles.” Money is rarely the primary motivator, but merely the trailing indicator of a life that finds its primary satisfaction in “beating the odds” or “pulling it off.” And every great business war story I’ve ever heard, like the story about sky-hiking above, is invariably a reverential tribute to pure audacity.

We hear a lot about the advantages that a life of “privilege” bestows on the children of the affluent: advantages denied to the underprivileged. There is much truth to this analysis, but in retrospect I owe much of my own success to my decidedly “underprivileged” background. I grew up in a 950 square foot house with my seven younger siblings. For years I firmly believed that the single bathroom we all shared had come prefabricated with someone insistently knocking on the door. We never ate out or went to the movies, and we shared a “party line” telephone with neighbors that seemed to share a talent for being on the phone whenever I wanted to use it. The one week vacation my hard working father took each summer was merely an opportunity to paint the house.

Yet the silver lining to my childhood is that my siblings and I had to learn how to hustle. Rather than playing organized little league baseball for example, I had to convince older boys to let me play in pick-up games; games they played on handmade fields with worn out baseballs and cracked bats wrapped in electrician’s tape. Hiding my glove in the bushes, I would pose as an innocent spectator until a right fielder with chores to do forced them to take a chance on a social inferior like me.

Most of life’s most important learning takes place in ancillary ways. These lessons are only tangentially related to the specific goal or task we are trying to accomplish. At the time my sky-hiking friend thought he was only trying to get from point A to point B as cheaply as possible. Similarly, I thought I was just trying to play baseball. But what we both were really doing was learning how to proactively use hustle to “make things happen:” an intangible character trait that every great leader must have.

For over 25 years I have mentored college students on a volunteer basis. Even taking into account maturity’s legendary disdain for the young, I still think the storehouse of hustle is gradually declining in our culture. My offers to help kids find jobs often go begging, and even when they don’t, the hungry hustle I am looking for is so often missing that I am reluctant to make introductions for fear of saddling a friend with an underachiever.

Though childless myself, I spent more than enough time changing the diapers of younger siblings to commiserate with today’s harried and often under-appreciated parents. But I still think that in our desire to make things “easier” for our kids, we risk robbing them of the challenges that produce one of life’s most important traits and ineffable pleasures: the ability to hustle.

I recently read in the Wall Street Journal that much of the apple harvest in the pacific North West is in danger of spoiling. Despite wages of $25-$30 an hour, the growers can’t find enough apple pickers to bring in their crop. Reading the article made me nostalgic for my vanished youth. When I was a young man I’d have taken the first bus west eager not only for the wages, but for the all the ancillary learning I could get from living among migrant workers and putting my character to the orchard test. But I’m still kicking myself because when I was young it never occurred to me to hitch a ride on a private plane rather than take the bus.